| Dan Matisoo | $50.00 |
| Joseph Onofaro | $50.00 |
| Paige McGlynn | |
|
Stephen Stachura |
$60.00 |
| 2025 | $190.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,083.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,444.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,205.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $3,405.00 | Reimagined |
| 2020 | $9,075.01 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,480.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,251.00 | Sturbridge to Provincetown Monument (2-Day) |
